EP0893119B1 - UV-protection formulation - Google Patents
UV-protection formulation Download PDFInfo
- Publication number
- EP0893119B1 EP0893119B1 EP98810688A EP98810688A EP0893119B1 EP 0893119 B1 EP0893119 B1 EP 0893119B1 EP 98810688 A EP98810688 A EP 98810688A EP 98810688 A EP98810688 A EP 98810688A EP 0893119 B1 EP0893119 B1 EP 0893119B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- sun protection
- protection agent
- oil
- absorber
- agent according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
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- 238000009472 formulation Methods 0.000 title claims description 35
- 230000006750 UV protection Effects 0.000 title description 8
- 239000006096 absorbing agent Substances 0.000 claims description 60
- 230000037072 sun protection Effects 0.000 claims description 32
- 239000000516 sunscreening agent Substances 0.000 claims description 29
- 239000011814 protection agent Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000003921 oil Substances 0.000 claims description 26
- 239000006185 dispersion Substances 0.000 claims description 25
- -1 triazine compound Chemical class 0.000 claims description 25
- 230000000475 sunscreen effect Effects 0.000 claims description 24
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
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- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229940057910 shea butter Drugs 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- ABTZKZVAJTXGNN-UHFFFAOYSA-N stearyl heptanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCC ABTZKZVAJTXGNN-UHFFFAOYSA-N 0.000 description 1
- 229940098758 stearyl heptanoate Drugs 0.000 description 1
- 229960000368 sulisobenzone Drugs 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/29—Titanium; Compounds thereof
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
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- A—HUMAN NECESSITIES
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- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
- A61K8/0279—Porous; Hollow
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/496—Triazoles or their condensed derivatives, e.g. benzotriazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4966—Triazines or their condensed derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
- A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
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- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/60—Particulates further characterized by their structure or composition
- A61K2800/65—Characterized by the composition of the particulate/core
- A61K2800/652—The particulate/core comprising organic material
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/60—Particulates further characterized by their structure or composition
- A61K2800/65—Characterized by the composition of the particulate/core
- A61K2800/654—The particulate/core comprising macromolecular material
Definitions
- the present invention relates to new UV-protection formulations which comprise a combination of a micronised UV absorber and both of i) an oil-soluble, non-micronised UV absorber and/or an inorganic micropigment and ii) a polymeric hollow sphere additive and/or a polymer selected from xanthan and/or polyvinylpyrrolidone.
- the new combinations exhibit an unexpected synergistic sun protection effect. This synergistic effect is greatly enhanced when the micronised UV absorber and the oil-soluble, non-micronised UV absorber and/or an inorganic micropigment are used in combination with a polymeric hollow sphere additive and/or a polymer selected from xanthan and/or polyvinylpyrrolidone.
- sunscreen formulations which include a material which is intended to counteract UV radiation, thereby inhibiting the said undesired effects on the skin.
- UV protectants in sunscreen formulations, especially soluble organic UV absorbers and insoluble micronised inorganic compounds, in particular zinc oxide and titanium dioxide.
- sunscreen formulations of soluble organic UV absorbers With respect to the use in sunscreen formulations of soluble organic UV absorbers, they have the disadvantages that their effectiveness as UV protectants in terms of SPF (Sun Protection Factor) in a sunscreen formulation is often too low for commercial purposes; as a result of their solubility, they exhibit relatively high allergenic potential; and that as a result of intrinsic photochemical lability, the duration of the protective effect is often too low.
- SPF Sun Protection Factor
- insoluble inorganic compounds such as titanium dioxide leads to a reduced stability of formulations containing them.
- inorganic compounds have been claimed to generate toxic radicals under the influence of light and water ("Redox Mechanisms in Heterogeneous Photocatalysis", Serpone et al, Electrochemistry in Colloids and Dispersions, Editors Mackay and Texter, VCH Publishers Inc., NewYork 1992).
- micronised, insoluble organic UV absorbers as well as a sunscreen composition
- a method of producing micronised, insoluble organic UV absorbers, as well as a sunscreen composition comprising a) 0.1 to 15%, preferably 0.5 to 10% by weight, based on the total composition of a micronised formulation of an insoluble organic UV absorber, produced according to the said method; and optionally b) a cosmetically acceptable carrier.
- Micronised, insoluble organic UV absorbers so obtained, when used in sunscreen formulations, provide excellent UV protection and have at least as high an SPF rating as corresponding sunscreen formulations containing a known inorganic UV absorber. Unlike the latter UV absorbers, micronised, insoluble organic UV absorbers show no tendency, under the influence of light, to generate radicals which could damage or sensitise human skin.
- the present invention provides, as a first aspect, a sun protection agent, which is especially suitable for use in pharmaceutical or cosmetic applications, comprising
- the relative proportions of components a):b) and/or c) preferably range from 20:80 to 80:20, especially from 40:60 to 60:40, by weight.
- the micronised organic UV absorber, component a) is preferably produced by the method described in GB-A-2303549, namely by a process which comprises grinding an organic UV absorber, in coarse particle form, in a grinding apparatus, in the presence of 1 to 50%, preferably 5 to 40% by weight, based on the micronised organic UV absorber, of an alkyl polyglucoside having the formula C n H 2n+1 O(C 6 H 10 O 5 ) x H, in which n is an integer ranging from 8 to 16 and x is the mean polymerisation level of the glucoside moiety (C 6 H 10 O 5 ) and ranges from 1.4 to 1.6, or an ester thereof.
- the grinding apparatus used to produce the micronised organic UV absorber may be, e.g., a jet, ball, vibration or hammer mill, preferably a high speed stirring mill or impact mill, especially a rotating ball mill, vibrating mill, tube mill or rod mill.
- the alkyl polyglucoside may consist of a C 1 -C 12 ester of the compound of formula C n H 2n+1 O(C 6 H 10 O 5 ) x H, namely an ester formed by reacting a C 1 -C 12 acid, such formic, acetic, propionic, butyric, sulfosuccinic, citric or tartaric acid, with one or more free OH groups on the glucoside moiety (C 6 H 10 O 5 ).
- a C 1 -C 12 acid such formic, acetic, propionic, butyric, sulfosuccinic, citric or tartaric acid
- the micronised organic UV absorber may be, e.g., a triazine, a benzotriazole, a vinyl group-containing amide, a cinnamic acid amide or a sulfonated benzimidazole UV absorber.
- Preferred compounds of formula (1) are those having one of the formulae as well as 2,4,6-tris(diisobutyl-4'-aminobenzalmalonate)-s-triazine and 2,4-bis(diisobutyl-4-aminobenzalmalonate)-6-(4'-aminobenzylidenecamphor)-s-triazine.
- Particularly preferred compounds of formula (1) are those having the formula in which the individual radicals R 5 are the same or different and each is hydrogen; an alkali metal; an ammonium group N(R 6 ) 4 in which R 6 is hydrogen or an organic radical; C 1 -C 3 alkyl; or a polyoxyethylene radical which contains from 1 to 10 ethylene oxide units and the terminal OH group of which may be etherified by a C 1 -C 3 alcohol.
- R 5 when R 5 is an alkali metal it is preferably potassium or, especially sodium; when R 5 is a group N(R 6 ) 4 in which R 6 has its previous significance, it is preferably a mono-, di- or tri-C 1 -C 4 alkylammonium salt, a mono-, di- or tri-C 2 -C 4 alkanolammonium salt or a C 1 -C 3 alkyl ester thereof; when R 6 is a C 1 -C 3 alkyl group, it is preferably a C 1 -C 2 alkyl group, more preferably a methyl group; and when R 6 is polyoxyethylene group, this preferably contains from 2-6 ethylene oxide units.
- T 1 is C 1 -C 3 alkyl or, preferably, hydrogen
- T 2 is C 1 -C 4 alkyl, preferably t-butyl, or C 1 -C 4 alkyl substituted by phenyl, preferably ⁇ , ⁇ -dimethylbenzyl.
- a further preferred class of triazole micronised organic UV absorbers is that having the formula in which T 2 is hydrogen; or C 1 -C 12 alkyl, preferably iso-octyl.
- a still further preferred class of triazole micronised organic UV absorbers is that having the formula in which T 2 is C 1 -C 12 alkyl, preferably iso-octyl.
- Preferred compounds of formula (28) are 4-methyl-3-penten-2-one, ethyl-3-methylamino-2-butenoate, 3-methylamino-1-phenyl-2-buten-1-one and 3-methylamino-1-phenyl-2-buten-1-one.
- a preferred class of cinnamic acid amide micronised organic UV absorbers is that having the formula in which R 12 is hydroxy or C 1 -C 4 alkoxy, preferably methoxy or ethoxy; R 13 is hydrogen or C 1 -C 4 alkyl, preferably methyl or ethyl; and R 14 is -(CONH) m -phenyl in which m has its previous significance and the phenyl group is optionally substituted by one, two or three substituents selected from OH, C 1 -C 3 alkyl, C 1 -C 3 alkoxy or CO-OR 4 in which R 4 has its previous significance.
- R 14 is phenyl, 4-methoxyphenyl or the phenylaminocarbonyl group.
- a preferred class of sulfonated benzimidazole micronised organic UV absorbers is that having the formula in which M is hydrogen or an alkali metal, preferably sodium, an alkaline earth metal, such as magnesium or calcium, or zinc.
- C 1 -C 12 alkyl groups may be methyl, ethyl, n-propyl or isopropyl, butyl, pentyl, amyl, isoamyl, hexyl, heptyl, octyl, iso-octyl, nonyl, decyl, undecyl oder dodecyl, methyl being preferred; and C 1 -C 3 alkoxy groups include methoxy, ethoxy, propoxy and isopropoxy, methoxy and ethoxy being preferred.
- C 2 -C 4 carboxyalkyl includes carboxymethyl, carboxyethyl, carboxypropyl and carboxyisopropyl, carboxymethyl being preferred.
- C 5 -C 8 cycloalkyl includes cyclopentyl, cyclohexyl and cyclooctyl.
- the micronised organic UV absorber, component a) of the new sun protection agent has a mean particle size in the range of from 0.01 to 2, more preferably from 0.02 to 1.5, especially from 0.05 to 1.0 ⁇ .
- the oil-soluble organic UV absorber, the component b) of the sun protection agent of the present invention may be any known oil-soluble organic UV absorber, especially those which are already approved and marketed for cosmetic use.
- oil-soluble organic UV absorbers are described, for instance, in “Sunscreens", Development, Evaluation and Regulatory Aspects, Eds.:N.J.Lowe and N.A.Shaath, M.Dekker Inc., New York and Basel, 1990; and Ken Klein, Encyclopedia of UV absorbers for sunscreen products, Cosmetics & Toiletries 107 45-64 (1992).
- the oil-soluble, non-micronised UV absorber may be, for example, a p-aminobenzoic acid derivative such as an ester, salt or an amine-modified derivative of p-aminobenzoic acid; a salicylic acid derivative such as an ester or salt thereof; a benzophenone derivative; a dibenzoylmethane derivative; a diphenylacrylate derivative; a benzofuran derivative; a polymeric UV absorber containing one or more silico-organic residues; a cinnamate ester; a camphor derivative; a trianilino-s-triazine derivative; phenylbenzimidazole sulfonic acid and its salts; urocanic acid (3-imidazol-4-yl-acrylic acid) or its ethyl ester; menthyl anthranilate; a benzotriazole; a hydroxyphenyltriazine derivative; or a bis-
- a p-aminobenzoic acid derivative examples include 4-aminobenzoic acid (PABA), ethyl dihydroxypropyl PABA having the formula
- PEG-25 PABA having the formula in which m, n and x are the same and each is approximately 25, octyl dimethyl PABA having the formula: and glyceryl aminobenzoate having the formula
- a salicylic acid derivative examples include homosalate (homomenthyl salicylate) having the formula triethanolamine salicylate having the formula amyl p-dimethylamino benzoate having the formula octyl salicylate having the formula 4-isopropylbenzylsalicylate having the formula
- benzophenone derivatives include benzophenone-3-(2-hydroxy-4-methoxybenzophenone), benzophenone-4 (2-hydroxy-4-methoxybenzophenone-5-sulfonic acid) and benzophenone-8-(2,2'-dihydroxy-4-methoxybenzophenone).
- a specific example of a dibenzoylmethane derivative is butyl methoxydibenzoylmethane [1-(4-tert.-butyl)-3-(4-methoxyphenyl)propane-1,3-dione].
- diphenylacrylate derivative examples include octocrylene (2-ethylhexyl-2-cyano-3,3'-diphenyl acrylate) and etocrylene (ethyl-2-cyano-3,3'-diphenyl acrylate).
- benzofuran derivative examples include the 3-(benzofuranyl)-2-cyanoacrylates described in US 5338539 or EP 582189, especially the compounds having the formula or the 2-(2-benzofuranyl)-5-tert.-butylbenzoxazoles described in US 5518713 and the 2-(p-aminophenyl)benzofurans described in US 5362481.
- a polymeric UV absorber containing one or more silico-organic residues are the benzylidenemalonate silicone derivatives disclosed in EP 709080, in particular the compound having the formula: in which R 15 is H or OMe and r is approximately 7; and the polymers of the benzotriazole silicone type described in WO 94/06404, in particular the compound having the formula:
- a cinnamate ester examples include octyl methoxy cinnamate (4-methoxycinnamic acid 2-ethylhexyl ester), diethanolamine methoxy cinnamate (diethanolamine salt of 4-methoxycinnamic acid), isoamyl p-methoxycinnamate (4-methoxycinnamic acid 2-isoamyl ester), 2,5-diisopropyl methyl cinnamate, the cinnamido derivatives disclosed in US 5601811 and the derivatives described in WO 97/00851.
- camphor derivatives are 4-methyl-benzylidene camphor [3-(4'-methyl)benzylidene-bornan-2-one], 3-benzylidene camphor (3-benzylidene-boman-2-one), polyacrylamidomethyl benzylidene camphor ⁇ N-[2(and 4)-2-oxybom-3-yliden-methyl)benzyl]acrylamide polymer ⁇ , trimonium benzylidene camphor sulfate [3-(4'-trimethylammonium)-benzylidene-bornan-2-one methyl sulfate], terephthalydene dicamphor sulfonic acid ⁇ 3,3'-(1,4-phenylenedimethine)-bis-(7,7-dimethyl-2-oxo-bicyclo-[2.2.1]heptan-1-methanesulfonic acid ⁇ and salts thereof and benzylidene camphor sulfonic acid [3-
- trianilino-s-triazine derivatives include octyl triazine [2,4,6-trianilino-(p-carbo-2'-ethyl-1'-oxy)-1,3,5-triazine, the trianilino-s-triazine derivatives disclosed in US 5332568, the trianilino-s-triazine derivatives described in EP 517104, trianilino-s-triazine derivatives disclosed in EP 570838, the trianilino-s-triazine derivatives described in US 5252323, the trianilino-s-triazine derivatives described in WO 93/17002-A1 and the trianilino-s-triazine derivatives disclosed in WO 97/03642-A1.
- a specific example of a benzotriazole is 2-(2-hydroxy-5-methyl-phenyl)benzotriazole.
- hydroxyphenyltriazine derivatives include, e.g. those described EP-A1-775,698, such as 2,4-bis- ⁇ [4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl ⁇ -6-(4-methoxyphenyl)-1,3,5-triazine.
- bis-resorcinol-dialkylaminotriazines are, e.g., those described in EP-A1-780,382.
- the inorganic micropigment UV absorber, the component b) of the new sun protection agent may be, for example, titanium dioxide coated with aluminium oxide or silicon dioxide, zinc oxide coated with aluminium oxide or silicon dioxide, or mica.
- the polymeric hollow sphere component, component c) of the new sun protection agent according to the present invention may be, for instance, those described in EP-A-761,201.
- the polymeric hollow sphere component is preferably a commercially available styrene/acrylic acid copolymer hollow sphere material.
- the styrene/acrylic acid copolymer is supplied as an aqueous dispersion comprising styrene/acrylic acid copolymer beads having a particle size below 1 micron.
- the said aqueous dispersion preferably has a solids content within the range of from 20 to 50%, more preferably from 25 to 45%, by weight; a voids volume of 15 to 60%, more preferably from 20 to 55%; a mean particle size of 0.1 to 5 microns, more preferably 0.1 to 1.5 microns; and a wall thickness of 0.01 to 1 micron, more preferably from 0.02 to 0.5 micron.
- the polymeric hollow sphere component may, of course, be derived from any suitable monomer and need not be limited to styrene/acrylic acid copolymer hollow sphere material.
- Suitable hollow sphere material are for example acrylonitrile copolymers, like copolymers of acrylonitrile with acrylic acid, methacrylic acid, styrene or vinylidene chloride.
- Preferred polymeric hollow sphere components are those which are substantially insoluble in cosmetic formulation components for sunscreens, since unduly high solubility therein can lead to an undesired decrease in the UV-protection performance of the resulting sunscreen formulation.
- the present invention also provides a sunscreen composition
- a sunscreen composition comprising A) 0.1 to 15%, preferably 0.5 to 10% by weight, based on the total composition of a sun screen agent according to the present invention; and B) a cosmetically acceptable carrier.
- the sunscreen composition of the present invention may be produced by physically blending the sun screen agent according to the present invention and a cosmetically acceptable carrier by any conventional method, e.g. by simply stirring the two materials together.
- the sunscreen composition of the invention may be formulated as a water-in oil or an oil-in-water dispersion, an oil or oil-alcohol lotion, a vesicular dispersion of an ionic or nonionic amphiphilic lipid, a gel, a solid stick or an aerosol formulation.
- the cosmetically acceptable carrier When formulated as a water-in oil or an oil-in-water dispersion, the cosmetically acceptable carrier preferably comprises 5 to 50% of an oil phase, 5 to 20% of an emulsifier and 30 to 90% of water, each by weight based on the total weight of the carrier.
- the oil phase may comprise any oil conventionally used in cosmetic formulations, especially an emollient e.g., one or more of a fatty alcohol; hydrocarbon oil; a natural or synthetic triglyceride; a wax including esters of long-chain acids and alcohols as well as compounds having wax-like properties; a silicone oil; a fatty acid ester or a fatty alcohol; and lanoline-containing products.
- an emollient e.g., one or more of a fatty alcohol; hydrocarbon oil; a natural or synthetic triglyceride; a wax including esters of long-chain acids and alcohols as well as compounds having wax-like properties; a silicone oil; a fatty acid ester or a fatty alcohol; and lanoline-containing products.
- fatty alcohols include cetyl alcohol, stearyl alcohol, octyldodecanol, cetearyl alcohol and oleyl alcohol;
- hydrocarbon oils are, e.g., mineral oil (light or heavy), petrolatum (yellow or white), polyethylene, paraffin, squalane, microcrystalline wax, ceresin, polybutene and hydrogenated polyisobutene;
- examples of a natural or synthetic triglyceride include castor oil, caprylic/capric triglyceride, Japan wax, hydrogenated vegetable oil, sweet almond oil, wheat germ oil, sesame oil, hydrogenated cottonseed oil, coconut oil, wheat germ glycerides, avocado oil, corn oil, trilaurin, hydrogenated castor oil, shea butter, cocoa butter, soybean oil, mink oil, sunflower oil, safflower oil, macadamia nut oil, olive oil, hydrogenated tallow, apricot kernel oil, hazelnut oil and borage oil; examples of
- examples of a fatty acid ester or a fatty alcohol include isopropyl myristate, isopropyl palmitate, octyl palmitate, isopropyl lanolate, acetylated lanolin alcohol, the benzoate of C 12 -C 15 alcohols, cetearyl octanoate, cetyl palmitate, myristyl myristate, myristyl lactate, cetyl acetate, propylene glycol dicaprylate/caprate, decyl oleate, acetylated lanolin, stearyl heptanoate, diisostearyl malate, octyl hydroxystearate, octyl hydroxystearate and isopropyl isostearate; and examples of lanoline-containing products include lanolin, lanolin oil, isopropyl lanolate, acetyl
- the emulsifier may comprise any emulsifier conventionally used in cosmetic formulations, e.g., one or more of an ethoxylated ester of a natural oil derivative such as a polyethoxylated ester of hydrogenated castor oil; a silicone oil emulsifier such as a silicone polyol; an optionally ethoxylated fatty acid soap; an ethoxylated fatty alcohol; an optionally ethoxylated sorbitan ester; an ethoxylated fatty add; or an ethoxylated glyceride.
- an ethoxylated ester of a natural oil derivative such as a polyethoxylated ester of hydrogenated castor oil
- silicone oil emulsifier such as a silicone polyol
- an optionally ethoxylated fatty acid soap an ethoxylated fatty alcohol
- an optionally ethoxylated sorbitan ester an ethoxylated fatty add
- the sunscreen composition of the invention may also comprise further components which are known to perform a useful function in a sunscreen composition.
- further components include, e.g., emollients, skin moisturisers, skin tanning accelerators, antioxidants, emulsion stabilisers, thickening agents such as xanthan, moisture-retention agents such as glycerine, film formers, preservatives, perfumes and colourants.
- the sunscreen composition of the invention provides excellent protection of the human against the damaging effects of sunlight, while permitting safe tanning of the skin. Moreover, the sunscreen composition of the invention has a skin waterproofing effect.
- aqueous dispersions of styrene/acrylic acid copolymer hollow spheres used in the following test methods have the following physical characteristics: Polymer solids content (%) voids volume (%) mean particle size (microns) wall thickness (microns) Ropaque HP-91 (I*) 27.5 50 1.0 0.1 Ropaque OP-84-2M (II*) 40.0 22 0.5 0.1 Ropaque OP-90 E (III*) 37.5 33 0.4 0.06
- oil-in-water cream A) oil phase composition: Tegin P 1.0% Thickly viscous paraffin oil 5.0% Stearic acid 1.5% Lanette O 0.4% Propyl paraben 0.1% Oil-soluble UVA (Parsol MCX) x%.
- Parsol MCX is octyl methoxycinnamate.
- Compound of formula (101) is 2,2'-methylene-bis-[6-(2H-benzotriazole-2-yl)-4-(1,1,3,3-tetramethylbutyl)-phenol]:
- the individual test formulations are produced as follows.
- the oil-soluble UVA (Parsol MCX) is dissolved in a specified amount (see following Table) in the oil phase.
- the aqueous micronised UVA (compound of formula (101)), optionally together with the polymer, is incorporated into the aqueous phase.
- the two phases are separately heated to 75°C. and then the oil phase is slowly stirred into the water phase and the whole mixture is stirred cold.
- the individual test formulations so obtained are then evaluated, in vitro, for their SPF performance using an SPF-290 analyser (Fa. Optometrics).
- SPF-290 analyser Fe. Optometrics
- Four brush strokes of each test formulation are applied, in a layer thickness of 2 ⁇ l/cm 2 on to Transpore film (3M) and 9 SPF measurements are conducted from each applied brush stroke.
- the SPF values obtained are shown in the following Table 1, together with the mean values and standard deviations, for each of the individual 36 measurements.
- the percentage amounts of of polymer shown in the Table 1 are based on the weight of active substance.
- Oil Phase 1 propylene glycol stearate 1.0% mineral oil 5.0% stearic acid 1.5% cetearyl alcohol 0.4% propylparaben 0.1% test oil-soluble UV absorber 2.7% Aqueous Phase 2 triethanolamine 0.8% glycerine (85%) 4.0% carbomer 0.1% methylparaben 0.1% water to 100%.
- Inorganic micropigment (micro-TiO 2 , silicon-coated) is incorporated (6.0% by weight based on the solids content of the total formulation) into the oil phase.
- Micronised test organic UV absorber is incorporated (6.0% by weight based on the solids content of the total formulation), as a suspension, into the aqueous phase.
- Phases 1 and 2 are separately heated to 75°C. With continuous stirring, the oil phase is added to the aqueous phase and, while homogenising, the mixture is cooled to 30°C.
- Example Test oil-soluble UVA (% by weight) Test micronised UVA (% by weight) SPF in vitro - 2.7% UVA I - 4.2 - - 6.0% by weight UVA II 7.7 - - 6.0% by weight silicon-coated TiO 2 4.8 14 2.7% UVA I 6.0% by weight UVA II 14.2 15 2.7% UVA I 6.0% by weight silicon-coated TiO 2 7.9
- UVA I is 2-ethylhexyl-p-methoxycinnamate and UVA II is a 25% aqueous dispersion of [2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine] having a mean particle size of 0.55 micron.
- UVA III is a 50% aqueous dispersion of [2,2'-methylene-bis-6(2H-benzotriazole-2-yl)-4-(1,1,3,3-teramethylbutyl)-phenol] having a mean particle size of 0.25 micron.
- UVA IV is 4-methyl-benzylidene camphor.
- a pre-dispersion A is produced consisting of a 50% aqueous dispersion of micronised UVA III.
- pre-dispersion B1 There are then added to pre-dispersion A, 2% of xanthan gum and 0.4% propylene glycol, to produce pre-dispersion B1. There are then added to pre-dispersion B1, 2.0% of polyvinylpyrrolidone (MW 8000) to produce pre-dispersion B2.
- the pre-dispersions A, B1 and B2 are then incorporated into separate samples of the same simple oil-in-water formulation and the final formulations are used for in vitro SPF determinations employing an SPF-analyser 290 (Optometrics). The evaluations are conducted using the method of Diffey & Robson (J.Soc.Cosmet. 40 127-133, 1989).
- phase 1 cetearyl alcohol Phase 1 cetearyl alcohol
- PEG-40 Castor oil
- sodium cetearyl sulfate mixt 3.15% decyl oleat 15.0% test oil-soluble UVA IV or V 4.0% propylparaben 0.1%
- Phase 2 50% aqueous dispersion of micronised UVA III 6 or 12% methylparaben 0.3% disodium EDTA 0.1% water 50.75 or 45.75%
- Phase 3 carbomer Carbopol 934P
- sodium hydroxide 45%
- Phase 1 is heated to 75-80°C.
- Phase 2 is heated to 80°C. while applying thorough homogenisation.
- Phase 1 is then added to phase 2, while applying continuous stirring.
- Phase 3 is then added to the mixture of phases 1 and 2, while applying continuous stirring, and then re-homogenised for 3 minutes. After replenishing water loss, the whole mixture is homogenised until it is cool.
- test formulations so obtained are then evaluated, in vitro, for their SPF performance using an SPF-290 analyser (Fa. Optometrics).
- SPF-290 analyser Fe. Optometrics
- Four brush strokes of each test formulation are applied, in a layer thickness of 2 ⁇ l/cm 2 on to Transpore film (3M) and 9 SPF measurements are conducted from each applied brush stroke.
- the SPF values obtained are shown in the following Table 7, together with the mean values and standard deviations, for each of the individual 36 measurements.
- UVA V is octyl-methoxycinnamate
- UVA VI is 3-(4-methylbenzidene)-boman-2-one
- UVA VII is 2,4,6-trianilino-p-(carbo-2'-ethylhexyl-1'-oxy)-1,3,5-triazine.
- Oil Phase isostearyl isostearate 4.0% caprylic/capric triglyceride 4.0% liquid paraffin 3.3% stearyl alcohol 1.4% cetyl alcohol 1.4% titanium dioxide (Eusolex T-2000) 4.0% dimethicone 1.0% propylparaben 0.1%
- the two phases are separately heated to 65°C. and then the oil phase is stirred into the aqueous phase and the whole mixture is stirred cold.
- the pH of the emulsion so obtained is adjusted to 6.5 to 7.0 and then the emulsion is evaluated, in vitro, to determine its SPF performance, using an SPF-290 analyser (Fa. Optometrics).
- the SPF value obtained is 21. When the experiment is repeated, but omitting the compound (26) from the aqueous phase, the SPF value is only 9.
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US8080257B2 (en) | 2000-12-12 | 2011-12-20 | L'oreal S.A. | Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using |
US7166274B2 (en) | 2000-12-18 | 2007-01-23 | L'oreal | Synergistically high SPF photoprotective UV-screening compositions comprising insoluble organic sunscreen particles/diarylbutadiene compounds |
US7749524B2 (en) | 2003-07-11 | 2010-07-06 | L'oreal S.A. | Cosmetic compositions comprising a structuring agent, silicone powder and swelling agent |
US7976831B2 (en) | 2004-04-02 | 2011-07-12 | L'oreal S.A. | Method for treating hair fibers |
US10219990B2 (en) | 2014-12-09 | 2019-03-05 | Basf Se | Solubilizing agents for UV filters in cosmetic formulations |
CN111867553A (zh) * | 2018-03-20 | 2020-10-30 | 帝斯曼知识产权资产管理有限公司 | 表面组合物 |
US11992544B2 (en) * | 2018-03-20 | 2024-05-28 | Dsm Ip Assets B.V. | Topical composition |
CN111867553B (zh) * | 2018-03-20 | 2024-06-07 | 帝斯曼知识产权资产管理有限公司 | 表面组合物 |
Also Published As
Publication number | Publication date |
---|---|
KR19990014129A (ko) | 1999-02-25 |
KR100541173B1 (ko) | 2006-07-11 |
AU741731B2 (en) | 2001-12-06 |
DE69817706T2 (de) | 2004-07-08 |
US6235271B1 (en) | 2001-05-22 |
JPH11100317A (ja) | 1999-04-13 |
AU7842998A (en) | 1999-02-04 |
IL125428A (en) | 2004-06-20 |
BRPI9802577B1 (pt) | 2017-04-18 |
GB9715751D0 (en) | 1997-10-01 |
IL125428A0 (en) | 1999-03-12 |
ID20611A (id) | 1999-01-28 |
DE69817706D1 (de) | 2003-10-09 |
ZA986622B (en) | 1999-01-26 |
JP4386483B2 (ja) | 2009-12-16 |
ES2205426T3 (es) | 2004-05-01 |
EP0893119A1 (en) | 1999-01-27 |
BR9802577A (pt) | 2000-12-19 |
CA2243553A1 (en) | 1999-01-26 |
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